Diisopropylethylamine → N-({4-bromo-2-[(trifluoromethyl)oxy]phenyl}methyl)-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide

HRID 1510953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510953
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[C:4]([O:10][C:11]([F:14])([F:13])[F:12])[CH:3]=1.[CH3:15][C:16]1[N:21]=[C:20]([NH:22][CH3:23])[N:19]=[C:18]([NH:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH:27]([C:31](O)=[O:32])[CH2:26]2)[N:17]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:31]([CH:27]2[CH2:28][CH2:29][CH2:30][CH:25]([NH:24][C:18]3[N:17]=[C:16]([CH3:15])[N:21]=[C:20]([NH:22][CH3:23])[N:19]=3)[CH2:26]2)=[O:32])=[C:4]([O:10][C:11]([F:12])([F:13])[F:14])[CH:3]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59447718(4-Bromo-2-(trifluoromethoxy)phenyl)methanamineHCID 594482213-{[4-Methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxylic acid

Produkt 1

HCID 67493268N-({4-bromo-2-[(trifluoromethyl)oxy]phenyl}methyl)-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of ({4-bromo-2-[(trifluoromethyl)oxy]phenyl}methyl)amine (0.4 g, 1.041 mmol), 3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxylic acid (0.276 g, 1.041 mmol), 1H-1,2,3-benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP reagent, 0.507 g, 1.146 mmol) and diisopropylethylamine (0.364 ml, 2.083 mmol) in N,N-Dimethylformamide (DMF) (5 ml) was stirred overnight at RT. The reaction mixture was treated with water which caused a precipitate to form. The precipitate was filtered and washed with water, and dried to give N-({4-bromo-2-[(trifluoromethyl)oxy]phenyl}methyl)-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide (0.35 g, 0.543 mmol, 53%) as an off-white solid. MS (ES) m/e 517, 519 [M+H]+.

Aufarbeitung

  1. customto form
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-aa1c126f0913448aa965ab20733d4d2b
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212032B2

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